NPASS Compound

Structure

NPC309300 OpenBabel07101719242D 21 22 0 0 1 0 0 0 0 0999 V2000 1.9935 -2.6696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3028 -3.0458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1300 -2.7389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6502 2.2863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9675 -0.2530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5094 -0.1672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3201 -1.1491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1377 0.7612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6582 -2.1086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7132 -1.7815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4843 -0.6440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9761 0.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4582 0.8888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0395 -2.3696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6300 -1.8728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3231 1.3413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8223 -1.3935 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0951 -0.9955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3243 1.3888 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0885 2.3606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 2 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 18 2 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 16 19 1 0 0 0 0 17 14 1 1 0 0 0 17 18 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	338.244
LogP:	4.435
LogD:	4.201
LogS:	-4.376
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.638
Synthetic Accessibility Score:	4.944
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.612
MDCK Permeability:	2.278739157191012e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.907
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.977
30% Bioavailability (F30%):	0.818

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.854
Plasma Protein Binding (PPB):	79.68578338623047%
Volume Distribution (VD):	1.173
Pgp-substrate:	17.848962783813477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.109
CYP1A2-substrate:	0.16
CYP2C19-inhibitor:	0.121
CYP2C19-substrate:	0.775
CYP2C9-inhibitor:	0.419
CYP2C9-substrate:	0.223
CYP2D6-inhibitor:	0.11
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.79
CYP3A4-substrate:	0.52

ADMET: Excretion

Clearance (CL):	11.057
Half-life (T1/2):	0.158

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.348
Drug-inuced Liver Injury (DILI):	0.061
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.73
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.303
Carcinogencity:	0.895
Eye Corrosion:	0.025
Eye Irritation:	0.033
Respiratory Toxicity:	0.973

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC309300

Natural Product ID:	NPC309300
*Common Name:**	(1S,3As,5S,9E,12Z)-3A,10-Dimethyl-6-Methylidene-1-Propan-2-Yl-1,2,3,4,5,7,8,11-Octahydrocyclopenta[11]Annulen-5-Ol
IUPAC Name:	(1S,3aS,5S,9E,12Z)-3a,10-dimethyl-6-methylidene-1-propan-2-yl-1,2,3,4,5,7,8,11-octahydrocyclopenta[11]annulen-5-ol
Synonyms:
Standard InCHIKey:	LVJSJETVMXBUIN-KDTINLHCSA-N
Standard InCHI:	InChI=1S/C20H32O/c1-14(2)17-11-12-20(5)13-19(21)16(4)8-6-7-15(3)9-10-18(17)20/h7,10,14,17,19,21H,4,6,8-9,11-13H2,1-3,5H3/b15-7+,18-10-/t17-,19-,20-/m0/s1
SMILES:	CC(C)[C@@H]1CC[C@@]2(C)C[C@@H](C(=C)CC/C=C(C)/C/C=C/12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472093
PubChem CID:	16091539
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001760] Dolabellane and neodolabellane diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO27081.1	Clavularia inflata	Under-species	n.a.	n.a.	n.a.	formosan soft coral	n.a.	PMID[17067152]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.6	ug ml-1	PMID[549799]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC309300 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1724
0.2-0.3	11667
0.3-0.4	13602
0.4-0.5	7523
0.5-0.6	5826
0.6-0.7	1827
0.7-0.8	357
0.8-0.85	16
0.85-0.9	9
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9194	High Similarity	NPC19569
0.9194	High Similarity	NPC477009
0.9194	High Similarity	NPC238352
0.8939	High Similarity	NPC471662
0.8769	High Similarity	NPC167527
0.8689	High Similarity	NPC5698
0.8615	High Similarity	NPC477791
0.8615	High Similarity	NPC136813
0.8571	High Similarity	NPC474480
0.8548	High Similarity	NPC323153
0.8485	Intermediate Similarity	NPC224532
0.8462	Intermediate Similarity	NPC162309
0.8438	Intermediate Similarity	NPC225415
0.8429	Intermediate Similarity	NPC310643
0.8429	Intermediate Similarity	NPC247325
0.8429	Intermediate Similarity	NPC244488
0.8413	Intermediate Similarity	NPC210346
0.8406	Intermediate Similarity	NPC471659
0.8387	Intermediate Similarity	NPC122239
0.8333	Intermediate Similarity	NPC114651
0.8281	Intermediate Similarity	NPC473759
0.8281	Intermediate Similarity	NPC474155
0.8281	Intermediate Similarity	NPC279200
0.8261	Intermediate Similarity	NPC14352
0.8261	Intermediate Similarity	NPC234527
0.8261	Intermediate Similarity	NPC474140
0.8254	Intermediate Similarity	NPC252809
0.8254	Intermediate Similarity	NPC471081
0.8235	Intermediate Similarity	NPC34834
0.8209	Intermediate Similarity	NPC160209
0.8194	Intermediate Similarity	NPC474216
0.8182	Intermediate Similarity	NPC272125
0.8154	Intermediate Similarity	NPC290367
0.8154	Intermediate Similarity	NPC287744
0.8154	Intermediate Similarity	NPC140233
0.8143	Intermediate Similarity	NPC469533
0.8143	Intermediate Similarity	NPC329090
0.8143	Intermediate Similarity	NPC27395
0.8143	Intermediate Similarity	NPC469593
0.8143	Intermediate Similarity	NPC469534
0.8125	Intermediate Similarity	NPC274704
0.8125	Intermediate Similarity	NPC225342
0.8095	Intermediate Similarity	NPC475931
0.8088	Intermediate Similarity	NPC167272
0.8088	Intermediate Similarity	NPC217570
0.8088	Intermediate Similarity	NPC471560
0.8088	Intermediate Similarity	NPC90115
0.8088	Intermediate Similarity	NPC269877
0.8082	Intermediate Similarity	NPC209430
0.8082	Intermediate Similarity	NPC28862
0.8082	Intermediate Similarity	NPC84694
0.8082	Intermediate Similarity	NPC143182
0.8082	Intermediate Similarity	NPC30986
0.8082	Intermediate Similarity	NPC47982
0.8082	Intermediate Similarity	NPC109546
0.8082	Intermediate Similarity	NPC81306
0.806	Intermediate Similarity	NPC68703
0.806	Intermediate Similarity	NPC69649
0.806	Intermediate Similarity	NPC472255
0.806	Intermediate Similarity	NPC472253
0.8028	Intermediate Similarity	NPC288035
0.8028	Intermediate Similarity	NPC257347
0.8028	Intermediate Similarity	NPC285893
0.8028	Intermediate Similarity	NPC304309
0.8028	Intermediate Similarity	NPC162742
0.8028	Intermediate Similarity	NPC230301
0.8028	Intermediate Similarity	NPC28657
0.8028	Intermediate Similarity	NPC328104
0.8028	Intermediate Similarity	NPC134847
0.8028	Intermediate Similarity	NPC22105
0.8028	Intermediate Similarity	NPC313185
0.8028	Intermediate Similarity	NPC471723
0.8028	Intermediate Similarity	NPC319090
0.8028	Intermediate Similarity	NPC136188
0.8028	Intermediate Similarity	NPC141071
0.8	Intermediate Similarity	NPC329763
0.7973	Intermediate Similarity	NPC324772
0.7973	Intermediate Similarity	NPC241290
0.7973	Intermediate Similarity	NPC209944
0.7973	Intermediate Similarity	NPC234193
0.7973	Intermediate Similarity	NPC164840
0.7971	Intermediate Similarity	NPC49422
0.7971	Intermediate Similarity	NPC9161
0.7969	Intermediate Similarity	NPC135648
0.7945	Intermediate Similarity	NPC473943
0.7945	Intermediate Similarity	NPC477514
0.7941	Intermediate Similarity	NPC208999
0.7941	Intermediate Similarity	NPC96484
0.7937	Intermediate Similarity	NPC226848
0.7937	Intermediate Similarity	NPC10017
0.7917	Intermediate Similarity	NPC107059
0.7917	Intermediate Similarity	NPC240604
0.7917	Intermediate Similarity	NPC113733
0.7917	Intermediate Similarity	NPC134330
0.7917	Intermediate Similarity	NPC202642
0.7917	Intermediate Similarity	NPC321016
0.7917	Intermediate Similarity	NPC321381
0.7917	Intermediate Similarity	NPC300324
0.7917	Intermediate Similarity	NPC237460
0.7917	Intermediate Similarity	NPC471658
0.7917	Intermediate Similarity	NPC470362
0.7917	Intermediate Similarity	NPC126969
0.7917	Intermediate Similarity	NPC189883
0.7917	Intermediate Similarity	NPC46160
0.7917	Intermediate Similarity	NPC129165
0.7917	Intermediate Similarity	NPC315261
0.7887	Intermediate Similarity	NPC306727
0.7887	Intermediate Similarity	NPC309178
0.7879	Intermediate Similarity	NPC300593
0.7867	Intermediate Similarity	NPC23852
0.7867	Intermediate Similarity	NPC209620
0.7867	Intermediate Similarity	NPC264245
0.7867	Intermediate Similarity	NPC320525
0.7857	Intermediate Similarity	NPC469343
0.7857	Intermediate Similarity	NPC471660
0.7857	Intermediate Similarity	NPC164045
0.7846	Intermediate Similarity	NPC475251
0.7826	Intermediate Similarity	NPC474248
0.7808	Intermediate Similarity	NPC34019
0.7808	Intermediate Similarity	NPC198968
0.7808	Intermediate Similarity	NPC318495
0.7808	Intermediate Similarity	NPC155986
0.7808	Intermediate Similarity	NPC214570
0.7794	Intermediate Similarity	NPC308522
0.7794	Intermediate Similarity	NPC74885
0.7778	Intermediate Similarity	NPC322353
0.7778	Intermediate Similarity	NPC278550
0.7778	Intermediate Similarity	NPC121744
0.7778	Intermediate Similarity	NPC118508
0.7778	Intermediate Similarity	NPC113639
0.7763	Intermediate Similarity	NPC296701
0.7763	Intermediate Similarity	NPC202389
0.7763	Intermediate Similarity	NPC218616
0.7763	Intermediate Similarity	NPC189972
0.7763	Intermediate Similarity	NPC49964
0.7763	Intermediate Similarity	NPC472465
0.7763	Intermediate Similarity	NPC50964
0.7763	Intermediate Similarity	NPC87489
0.7763	Intermediate Similarity	NPC101462
0.7761	Intermediate Similarity	NPC308844
0.7761	Intermediate Similarity	NPC61503
0.7746	Intermediate Similarity	NPC474743
0.7746	Intermediate Similarity	NPC130665
0.7746	Intermediate Similarity	NPC472506
0.7727	Intermediate Similarity	NPC211291
0.7727	Intermediate Similarity	NPC133368
0.7727	Intermediate Similarity	NPC473508
0.7714	Intermediate Similarity	NPC145498
0.7714	Intermediate Similarity	NPC254845
0.7714	Intermediate Similarity	NPC470041
0.7703	Intermediate Similarity	NPC244385
0.7703	Intermediate Similarity	NPC6978
0.7703	Intermediate Similarity	NPC76931
0.7703	Intermediate Similarity	NPC18603
0.7703	Intermediate Similarity	NPC87604
0.7703	Intermediate Similarity	NPC167037
0.7703	Intermediate Similarity	NPC302041
0.7703	Intermediate Similarity	NPC477522
0.7703	Intermediate Similarity	NPC138621
0.7703	Intermediate Similarity	NPC205455
0.7703	Intermediate Similarity	NPC186191
0.7703	Intermediate Similarity	NPC275910
0.7703	Intermediate Similarity	NPC65897
0.7703	Intermediate Similarity	NPC307965
0.7703	Intermediate Similarity	NPC85346
0.7703	Intermediate Similarity	NPC285761
0.7692	Intermediate Similarity	NPC47840
0.7692	Intermediate Similarity	NPC66020
0.7692	Intermediate Similarity	NPC234264
0.7692	Intermediate Similarity	NPC99487
0.7681	Intermediate Similarity	NPC471238
0.7671	Intermediate Similarity	NPC265588
0.7671	Intermediate Similarity	NPC73875
0.7671	Intermediate Similarity	NPC469646
0.7662	Intermediate Similarity	NPC474634
0.7662	Intermediate Similarity	NPC317458
0.7662	Intermediate Similarity	NPC320548
0.7662	Intermediate Similarity	NPC475789
0.7662	Intermediate Similarity	NPC470384
0.7656	Intermediate Similarity	NPC181872
0.7656	Intermediate Similarity	NPC475830
0.7656	Intermediate Similarity	NPC155025
0.7647	Intermediate Similarity	NPC202017
0.7647	Intermediate Similarity	NPC267027
0.7647	Intermediate Similarity	NPC476406
0.7647	Intermediate Similarity	NPC149680
0.7647	Intermediate Similarity	NPC279434
0.7639	Intermediate Similarity	NPC476366
0.7639	Intermediate Similarity	NPC201048
0.7632	Intermediate Similarity	NPC471661
0.7632	Intermediate Similarity	NPC47761
0.7632	Intermediate Similarity	NPC7505
0.7632	Intermediate Similarity	NPC82986
0.7632	Intermediate Similarity	NPC474731
0.7632	Intermediate Similarity	NPC474759
0.7632	Intermediate Similarity	NPC474752
0.7632	Intermediate Similarity	NPC474683
0.7619	Intermediate Similarity	NPC48891
0.7612	Intermediate Similarity	NPC107540
0.7612	Intermediate Similarity	NPC96793

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC309300 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	2387
0.2-0.3	4278
0.3-0.4	1655
0.4-0.5	377
0.5-0.6	224
0.6-0.7	56
0.7-0.8	27
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8143	Intermediate Similarity	NPD6926	Approved
0.8143	Intermediate Similarity	NPD6924	Approved
0.8088	Intermediate Similarity	NPD6922	Approved
0.8088	Intermediate Similarity	NPD6923	Approved
0.8082	Intermediate Similarity	NPD6929	Approved
0.8028	Intermediate Similarity	NPD6942	Approved
0.8028	Intermediate Similarity	NPD7339	Approved
0.7973	Intermediate Similarity	NPD6931	Approved
0.7973	Intermediate Similarity	NPD6930	Phase 2
0.7971	Intermediate Similarity	NPD7143	Approved
0.7971	Intermediate Similarity	NPD7144	Approved
0.7917	Intermediate Similarity	NPD6933	Approved
0.7857	Intermediate Similarity	NPD7150	Approved
0.7857	Intermediate Similarity	NPD7151	Approved
0.7857	Intermediate Similarity	NPD7152	Approved
0.7808	Intermediate Similarity	NPD5776	Phase 2
0.7808	Intermediate Similarity	NPD6925	Approved
0.7703	Intermediate Similarity	NPD7145	Approved
0.7662	Intermediate Similarity	NPD6695	Phase 3
0.7564	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7514	Phase 3
0.75	Intermediate Similarity	NPD7525	Registered
0.7468	Intermediate Similarity	NPD6893	Approved
0.7467	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD342	Phase 1
0.7432	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6902	Approved
0.7361	Intermediate Similarity	NPD4243	Approved
0.7333	Intermediate Similarity	NPD6932	Approved
0.7313	Intermediate Similarity	NPD368	Approved
0.7297	Intermediate Similarity	NPD8264	Approved
0.7284	Intermediate Similarity	NPD7524	Approved
0.7284	Intermediate Similarity	NPD7750	Discontinued
0.7273	Intermediate Similarity	NPD7509	Discontinued
0.7273	Intermediate Similarity	NPD7332	Phase 2
0.7179	Intermediate Similarity	NPD6898	Phase 1
0.7162	Intermediate Similarity	NPD4785	Approved
0.7162	Intermediate Similarity	NPD4784	Approved
0.7143	Intermediate Similarity	NPD6683	Phase 2
0.7125	Intermediate Similarity	NPD4786	Approved
0.7073	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5362	Discontinued
0.7	Intermediate Similarity	NPD5331	Approved
0.7	Intermediate Similarity	NPD5332	Approved
0.6962	Remote Similarity	NPD4790	Discontinued
0.6941	Remote Similarity	NPD7087	Discontinued
0.6923	Remote Similarity	NPD7645	Phase 2
0.6875	Remote Similarity	NPD3667	Approved
0.6842	Remote Similarity	NPD5275	Approved
0.6842	Remote Similarity	NPD4190	Phase 3
0.6835	Remote Similarity	NPD4822	Approved
0.6835	Remote Similarity	NPD4820	Approved
0.6835	Remote Similarity	NPD4821	Approved
0.6835	Remote Similarity	NPD4819	Approved
0.6818	Remote Similarity	NPD4219	Approved
0.6795	Remote Similarity	NPD4271	Approved
0.6795	Remote Similarity	NPD4268	Approved
0.6747	Remote Similarity	NPD5279	Phase 3
0.6707	Remote Similarity	NPD3133	Approved
0.6707	Remote Similarity	NPD3665	Phase 1
0.6707	Remote Similarity	NPD3666	Approved
0.6706	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6627	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4748	Discontinued
0.6625	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD4265	Approved
0.6552	Remote Similarity	NPD7637	Suspended
0.6552	Remote Similarity	NPD6079	Approved
0.6548	Remote Similarity	NPD3618	Phase 1
0.65	Remote Similarity	NPD4195	Approved
0.6437	Remote Similarity	NPD7136	Phase 2
0.6437	Remote Similarity	NPD5785	Approved
0.6429	Remote Similarity	NPD5363	Approved
0.642	Remote Similarity	NPD4252	Approved
0.642	Remote Similarity	NPD5368	Approved
0.6386	Remote Similarity	NPD7154	Phase 3
0.6364	Remote Similarity	NPD4732	Discontinued
0.6353	Remote Similarity	NPD5786	Approved
0.6341	Remote Similarity	NPD5369	Approved
0.6322	Remote Similarity	NPD4753	Phase 2
0.6292	Remote Similarity	NPD4202	Approved
0.6292	Remote Similarity	NPD6399	Phase 3
0.6265	Remote Similarity	NPD4221	Approved
0.6265	Remote Similarity	NPD4223	Phase 3
0.6265	Remote Similarity	NPD6435	Approved
0.6237	Remote Similarity	NPD7639	Approved
0.6237	Remote Similarity	NPD7640	Approved
0.6235	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD5329	Approved
0.619	Remote Similarity	NPD4788	Approved
0.6136	Remote Similarity	NPD6051	Approved
0.6129	Remote Similarity	NPD7638	Approved
0.6125	Remote Similarity	NPD1346	Approved
0.6118	Remote Similarity	NPD4197	Approved
0.6118	Remote Similarity	NPD3668	Phase 3
0.6118	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5211	Phase 2
0.6092	Remote Similarity	NPD4250	Approved
0.6092	Remote Similarity	NPD4251	Approved
0.6087	Remote Similarity	NPD5222	Approved
0.6087	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4697	Phase 3
0.6087	Remote Similarity	NPD5221	Approved
0.6022	Remote Similarity	NPD5173	Approved
0.6022	Remote Similarity	NPD4755	Approved
0.6022	Remote Similarity	NPD6083	Phase 2
0.6022	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD7331	Phase 2
0.6	Remote Similarity	NPD7515	Phase 2
0.6	Remote Similarity	NPD6411	Approved
0.5979	Remote Similarity	NPD5141	Approved
0.5978	Remote Similarity	NPD4629	Approved
0.5978	Remote Similarity	NPD5210	Approved
0.5977	Remote Similarity	NPD4249	Approved
0.5977	Remote Similarity	NPD4623	Approved
0.5977	Remote Similarity	NPD4688	Approved
0.5977	Remote Similarity	NPD4694	Approved
0.5977	Remote Similarity	NPD5330	Approved
0.5977	Remote Similarity	NPD4519	Discontinued
0.5977	Remote Similarity	NPD6409	Approved
0.5977	Remote Similarity	NPD4689	Approved
0.5977	Remote Similarity	NPD7334	Approved
0.5977	Remote Similarity	NPD7146	Approved
0.5977	Remote Similarity	NPD4693	Phase 3
0.5977	Remote Similarity	NPD5205	Approved
0.5977	Remote Similarity	NPD5280	Approved
0.5977	Remote Similarity	NPD4690	Approved
0.5977	Remote Similarity	NPD7521	Approved
0.5977	Remote Similarity	NPD4138	Approved
0.5977	Remote Similarity	NPD5690	Phase 2
0.5977	Remote Similarity	NPD6684	Approved
0.5972	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD4225	Approved
0.5938	Remote Similarity	NPD384	Approved
0.5938	Remote Similarity	NPD385	Approved
0.5934	Remote Similarity	NPD5779	Approved
0.5934	Remote Similarity	NPD5778	Approved
0.593	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD4700	Approved
0.5895	Remote Similarity	NPD4696	Approved
0.5895	Remote Similarity	NPD5285	Approved
0.5895	Remote Similarity	NPD5286	Approved
0.5867	Remote Similarity	NPD7341	Phase 2
0.5867	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD1696	Phase 3
0.5843	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD6903	Approved
0.5843	Remote Similarity	NPD4723	Approved
0.5843	Remote Similarity	NPD4722	Approved
0.5843	Remote Similarity	NPD6672	Approved
0.5843	Remote Similarity	NPD5737	Approved
0.5843	Remote Similarity	NPD4518	Approved
0.5833	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4695	Discontinued
0.5833	Remote Similarity	NPD5223	Approved
0.5806	Remote Similarity	NPD5695	Phase 3
0.5806	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5290	Discontinued
0.5783	Remote Similarity	NPD3617	Approved
0.5778	Remote Similarity	NPD6101	Approved
0.5778	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD5370	Suspended
0.5773	Remote Similarity	NPD5225	Approved
0.5773	Remote Similarity	NPD4633	Approved
0.5773	Remote Similarity	NPD5224	Approved
0.5773	Remote Similarity	NPD5226	Approved
0.5769	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD4139	Approved
0.5765	Remote Similarity	NPD4692	Approved
0.5765	Remote Similarity	NPD857	Phase 3
0.5758	Remote Similarity	NPD5739	Approved
0.5758	Remote Similarity	NPD6640	Phase 3
0.5758	Remote Similarity	NPD7333	Discontinued
0.5758	Remote Similarity	NPD6402	Approved
0.5758	Remote Similarity	NPD7128	Approved
0.5758	Remote Similarity	NPD6675	Approved
0.5733	Remote Similarity	NPD3197	Phase 1
0.5714	Remote Similarity	NPD5175	Approved
0.5714	Remote Similarity	NPD4754	Approved
0.5714	Remote Similarity	NPD5174	Approved
0.5714	Remote Similarity	NPD4096	Approved
0.5714	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7838	Discovery
0.5699	Remote Similarity	NPD7748	Approved
0.5699	Remote Similarity	NPD5282	Discontinued
0.5698	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD4787	Phase 1
0.5686	Remote Similarity	NPD6371	Approved
0.5676	Remote Similarity	NPD4194	Approved
0.5676	Remote Similarity	NPD4193	Approved
0.5676	Remote Similarity	NPD4192	Approved
0.5676	Remote Similarity	NPD4191	Approved
0.5658	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD8034	Phase 2
0.5652	Remote Similarity	NPD5284	Approved
0.5652	Remote Similarity	NPD7983	Approved
0.5652	Remote Similarity	NPD5281	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data